Enantioselective synthesis of L- and D-carboranylalanine

被引：46

作者：

Radel, PA ^{[1
]}

Kahl, SB ^{[1
]}

机构：

[1] UNIV CALIF SAN FRANCISCO,DEPT PHARMACEUT CHEM,SAN FRANCISCO,CA 94143

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 14期

关键词：

D O I：

10.1021/jo952271b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of L- and D-carboranylalanine is reported. Imides 13 and 14 are treated with titanium tetrachloride, DIEA, and NBS to introduce a bromo functionality in 98:2 ratio at the alpha-center. Azide displacement with TMGA, displacement of the oxazolidinone template with titanium tetrabenzyloxide, and subsequent hydrogenolysis permits L- or D-carboranylalanine to be isolated in high stereoselectivity and 35-40% yields overall.

引用

页码：4582 / 4588

页数：7

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